Réaction #937918

Équation de réaction

10-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

potassium carbonate

i-propyl bromoacetate

→

title compound

Rendement 59.0%

10-bromo-2-i-propoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

Rendement 59.0%

Solvants

dimethyl sulfoxide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 12 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   LavageThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   Autrethe solvent was evaporated under reduced pressure
6. 6
   AutreThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride containing 3% methanol)
7. 7
   Lavagethe crude product was washed with ether
8. 8
   Filtrationa small amount of methanol in succession, and recovered by filtration

Mode opératoire

10-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (3.6 g) obtained in Example 2 was suspended in dimethyl sulfoxide (200 ml), and to the suspension was added potassium carbonate (2.5 g), and the mixture was stirred at room temperature for 30 minutes. i-propyl bromoacetate (1.4 ml) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (300 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: methylene chloride containing 3% methanol), and the crude product was washed with ether and a small amount of methanol in succession, and recovered by filtration to obtain the title compound (2.6 g, 59%).

Source